# Your most painfully beautiful song **URL:** \ **Category:** Cafe Society\ **Created:** [January 31, 2008, 9:11am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698 "2008-01-31T09:11:45Z")\ **Posts on this page:** 20\ **Page:** 1
**Author:** ![Grey\_area](https://avatars.discourse-cdn.com/v4/letter/g/c5a1d2/32.png) [@Grey\_area](https://boards.straightdope.com/u/Grey_area)\ **Post date:** [January 31, 2008, 9:11am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/1 "2008-01-31T09:11:45Z")
I’m almost embarrassed to start this thread, but what I mean are those songs that would bring a tear to your eye if you were in that sort of sentimental mood. One for me is [Autumn Leaves](http://www.youtube.com/watch?v=K7-haKkFnT8), Eva Cassidy’s rendition in particular. [엄마야 누나야](http://www.seelotus.com/gojeon/hyeon-dae/si/si-new/em-ma-ya-nu-na-ya.htm) (Mom and sister) is another one. It’s based on a Korean poem about a young boy naively suggesting to his mother and sister they live by the river. I can’t quite figure out if I feel this way about the song because it was a favorite song of mine when I was little kid (which I’ve recently rediscovered) or something else entirely. ---
**Author:** ![jjimm](https://avatars.discourse-cdn.com/v4/letter/j/ba8739/32.png) [@jjimm](https://boards.straightdope.com/u/jjimm)\ **Post date:** [January 31, 2008, 9:46am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/2 "2008-01-31T09:46:15Z")
[Oh I’m missing you](http://www.youtube.com/watch?v=9B3P_qnxiEc) by Christy Moore - the song of a derelict Irish alcoholic, stuck in London because of the shame of returning home as a failure. Gets me every time. ---
**Author:** ![Dunderman](https://avatars.discourse-cdn.com/v4/letter/d/ecb155/32.png) [@Dunderman](https://boards.straightdope.com/u/Dunderman)\ **Post date:** [January 31, 2008, 10:04am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/3 "2008-01-31T10:04:58Z")
_Guldet blev till sand_, a Swedish song from the musical _Kristina från Duvemåla_. It concerns a Swedish immigrant to America who goes west in search for gold and persuades a friend - a rather simple-minded fellow - to come with him. They starve and thirst and the friend begs him to go back, but he refuses. His friend drinks water from a stagnant, stinking pond and dies. Eventually he returns, bringing only his friend’s pocket watch. ---
**Author:** ![Drain\_Bead](https://avatars.discourse-cdn.com/v4/letter/d/e47774/32.png) [@Drain\_Bead](https://boards.straightdope.com/u/Drain_Bead)\ **Post date:** [January 31, 2008, 2:06pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/4 "2008-01-31T14:06:58Z")
“Lover, You Should’ve Come Over” by Jeff Buckley ---
**Author:** ![BaneSidhe](https://avatars.discourse-cdn.com/v4/letter/b/c5a1d2/32.png) [@BaneSidhe](https://boards.straightdope.com/u/BaneSidhe)\ **Post date:** [January 31, 2008, 2:15pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/5 "2008-01-31T14:15:12Z")
“The River” by Garth Brooks. ---
**Author:** ![don\_t\_ask](https://avatars.discourse-cdn.com/v4/letter/d/e68b1a/32.png) [@don\_t\_ask](https://boards.straightdope.com/u/don_t_ask)\ **Post date:** [January 31, 2008, 2:18pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/6 "2008-01-31T14:18:13Z")
Easy: [Three Babies](http://www.youtube.com/watch?v=h3mQYj86JRM) by Sinead O’Connor I can put the headphones on, crank it up and cry for hours any time I like. But it’s my dead baby she is singing about. ---
**Author:** ![SaharaTea](https://avatars.discourse-cdn.com/v4/letter/s/e9a140/32.png) [@SaharaTea](https://boards.straightdope.com/u/SaharaTea)\ **Post date:** [January 31, 2008, 2:28pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/7 "2008-01-31T14:28:55Z")
Jeff Buckley’s “Hallelujah.” ---
**Author:** ![Wee\_Bairn](https://avatars.discourse-cdn.com/v4/letter/w/90db22/32.png) [@Wee\_Bairn](https://boards.straightdope.com/u/Wee_Bairn)\ **Post date:** [January 31, 2008, 2:30pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/8 "2008-01-31T14:30:24Z")
“Bonny”- Prefab Sprout ---
**Author:** ![phungi](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/phungi/32/395_2.png) [@phungi](https://boards.straightdope.com/u/phungi)\ **Post date:** [January 31, 2008, 2:31pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/9 "2008-01-31T14:31:03Z")
_Footsteps_ by Pearl Jam: [video](http://www.youtube.com/watch?v=XwM4I7Ii158) | [lyrics](http://www.theskyiscrape.com/website/wikijam/index.php/Footsteps) ---
**Author:** ![Gail](https://avatars.discourse-cdn.com/v4/letter/g/b9e5f3/32.png) [@Gail](https://boards.straightdope.com/u/Gail)\ **Post date:** [January 31, 2008, 3:16pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/10 "2008-01-31T15:16:57Z")
_Talk of the Town_ by the Pretenders…wistful, about unrequited love, and makes me wish I could sing like Chrissie Hynde [lyrics](http://www.lyricsfreak.com/p/pretenders/talk+of+the+town_20110700.html) ---
**Author:** ![RikWriter](https://avatars.discourse-cdn.com/v4/letter/r/49beb7/32.png) [@RikWriter](https://boards.straightdope.com/u/RikWriter)\ **Post date:** [January 31, 2008, 3:21pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/11 "2008-01-31T15:21:24Z")
Homeward Bound…the Mormon Tabernacle Choir version is beautiful, but I prefer the Navy Band Sea Chanter’s version personally. ---
**Author:** ![elfkin477](https://avatars.discourse-cdn.com/v4/letter/e/a9a28c/32.png) [@elfkin477](https://boards.straightdope.com/u/elfkin477)\ **Post date:** [January 31, 2008, 3:33pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/12 "2008-01-31T15:33:37Z")
Lovedrug “Happy Apple Poison” download it 1/3 down the page [here](http://puddlegum.net/march-2007-album-releases) I can’t quite explain why, but there’s something about the melody and the tone of the backing vocals, not the lyrics, that feels like heartbreak every time I listen to it. ---
**Author:** ![WomanofScorn](https://avatars.discourse-cdn.com/v4/letter/w/b5a626/32.png) [@WomanofScorn](https://boards.straightdope.com/u/WomanofScorn)\ **Post date:** [January 31, 2008, 3:45pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/13 "2008-01-31T15:45:21Z")
This song doesn’t make me cry but it does hit me for some reason. [The Queen and the Soldier](http://www.youtube.com/watch?v=Dt0sXRBLfJM) by Suzanne Vega ---
**Author:** ![Liberal](https://avatars.discourse-cdn.com/v4/letter/l/848f3c/32.png) [@Liberal](https://boards.straightdope.com/u/Liberal)\ **Post date:** [January 31, 2008, 3:47pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/14 "2008-01-31T15:47:46Z")
Two for me: **Angel** - Sarah McLachlan, played at our grandson’s funeral **Little Drummer Boy** - After the homeless vet episode of _West Wing_, this song is painfully beautiful ---
**Author:** ![Spice\_Weasel](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/spice_weasel/32/5435_2.png) [@Spice\_Weasel](https://boards.straightdope.com/u/Spice_Weasel)\ **Post date:** [January 31, 2008, 3:57pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/15 "2008-01-31T15:57:22Z")
Okay, so I assume we’re to go for the most humiliating song that moves us to tears. For me, this would be the song ‘‘Now That I’m a Woman’’ from _The Last Unicorn._ Yes, this song is in fact about a unicorn’s reaction to being transformed into a woman. At least, that’s what it’s about when you see it as a little girl. The entire movie is a sort of epic metaphor for the risk and regret inherent in adulthood, along the same lines of _Alice’s Adventures in Wonderland._ So I watch it, I remember a time when I didn’t realize what it was about, and I cry. _Once, I can’t remember I was long ago someone strange I was innocent and wise and full of pain Now that I’m a woman Everything has changed…_ [There you go.](http://www.youtube.com/watch?v=KByKoAks8XM) _slinks away in shame_ I second _Little Drummer Boy._ That song tears my shit up… and I’ve never seen West Wing. ---
**Author:** ![WordMan](https://avatars.discourse-cdn.com/v4/letter/w/e8c25b/32.png) [@WordMan](https://boards.straightdope.com/u/WordMan)\ **Post date:** [January 31, 2008, 3:58pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/16 "2008-01-31T15:58:02Z")
[QUOTE=SaharaTea] Jeff Buckley’s “Hallelujah.” [/QUOTE] I do love this version, too. However, I must offer a different one for this category: [Tabula Rasa by Arvo Part](http://www.amazon.com/Tabula-Rasa-Arvo-Part/dp/B0000262K7/ref=sr_1_1?ie=UTF8&s=music&qid=1201794868&sr=1-1) (Amazon link). It is a modern classical piece for strings (cello’s mostly) that was featured in a New Yorker piece. They described how terminally patients tend to gravitate towards it because it has the complexity of sadness mingled with the optimism of arrival - they call it the music of the angels. It immediately came to mind as perfectly fitting the OP. ---
**Author:** ![Exapno\_Mapcase](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/exapno_mapcase/32/1051_2.png) [@Exapno\_Mapcase](https://boards.straightdope.com/u/Exapno_Mapcase)\ **Post date:** [January 31, 2008, 4:16pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/17 "2008-01-31T16:16:56Z")
“A Summer Song,” by Chad & Jeremy. The song for everyone who’s ever had a summer love. ---
**Author:** ![Terraplane](https://avatars.discourse-cdn.com/v4/letter/t/74df32/32.png) [@Terraplane](https://boards.straightdope.com/u/Terraplane)\ **Post date:** [January 31, 2008, 4:18pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/18 "2008-01-31T16:18:50Z")
‘Jezebel’ by Iron + Wine [![](https://img.youtube.com/vi/ghBJhGIcneU/hqdefault.jpg "Iron & Wine - Jezebel") ](https://www.youtube.com/watch?v=ghBJhGIcneU) It’s a bad quality fan video (though the music sounds ok) so it takes a second for them to start the song, but it’s worth a listen if you haven’t heard it. ---
**Author:** ![MrDibble](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/mrdibble/32/114_2.png) [@MrDibble](https://boards.straightdope.com/u/MrDibble)\ **Post date:** [January 31, 2008, 4:24pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/19 "2008-01-31T16:24:41Z")
Tossup between Sting’s _Fragile_, Peter Gabriel’s _Biko_, Gabriel & Kate Bush’s _Don’t Give Up_, Shelleyan Orphan’s _Century Flower_, or This Mortal Coil’s _Mr Somewhere_ or _The Jeweller_. Right now, it’s Shelleyan Orphan, but tomorrow - who knows. ---
**Author:** ![chocolatefrog](https://avatars.discourse-cdn.com/v4/letter/c/41988e/32.png) [@chocolatefrog](https://boards.straightdope.com/u/chocolatefrog)\ **Post date:** [January 31, 2008, 4:29pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/20 "2008-01-31T16:29:23Z")
_Waltz #2_, by Elliot Smith [Next page](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698.md?page=2)